Manufacture and production of oxycarboxydiarylcarbinols.



UNITED STATES PATENT oFmoE.

MAX WEILER, 0F ELBERFELD, GERMANY, ASSIGNOR TO. FABBENFABRIKEN VORM. FRIEDR. BAYER, & 00., 0F ELBERFELD, GERMANY, A CQRBORATION 0F GERMANY.

MANUFACTURE AND PRODUQTIIDN: OF OXYCARBOXYDIARYLCARBINOLS.

No Drawing.

Specification of Letters Patent.

Application filed October 15, 1912. Serial No. $25 364.

' Patented Dee.3o,1913.

R' oHoH, n where R 'is an aromatic radical and R an The brownish melt is then poured on ice and the hydrol which separates is filtered ofi. The leuco acid obtained by condensation of this hydrol with ortho-cresotinic acid, yields, when oxidized, a'dyestufl producing on wool after chroming violet shades. v Instead of the above mentioned aldehyde other aldehydes, such as ortho-chloro-paradiethylaminobenzaldehyde, ortho chlorobenzaldehyde, poly chlorobenzaldehydes, sulfobenzald'ehyde, etc, can be used.

The oxyacid of the example can be replaced by other oxyacids e. g. metaor paracresotinic acid, 3-methyl-2-oxy-c-chlorobenzoic acid, 2-naphthol-3-carboxylic acid and their monosulfonic acids, etc. The condensation can also be performed in other Ways, for instance by heating with sulfuric acid (50 per cent-.), with alcoholic sulfuric acid or with other condensing agents.

I claim 1 p 1. As new products the new oxycarboxydiarylcarbinols obtained by condensing in equal molecular proportions aromatic aldehydes with aromatic oxycarboxylic acids and containing both a hydroxyl and a cararomatic oxycarboxylic acid radical, which yi en on nsed w rth molecule of a suitable aromatic oxycai boxylic acid leucotriarylmethane bodies, capable of dyestulfs.

In order to illustrate the new process more fully the following example is given, the parts being b Weight 17.7 parts of paradiethylamino enzaldehyde are dissolved in 250 parts of sulfuric acid (GO-66 B.) and 16.6 parts of s-xylenol-ortho-carboxylic acid (M. P. 166; obtainedfroms-xylenol-sodium and carbonic acid) are added to this solution while it is being stirred and cooled.

The reaction proceeds as illustrated by the following graphic equation:

boxyl group in the same aryl nucleus, which products are after being dried and pulverwhen condensed with a further molecule of an aromatic oxycarboxylic acid leucotriphenylmethane bodies capable of being converted by oxidation into mordant dyestufls, substantially as. described.

2. As new products the oxycarboxydiaryloarbinols obtainable by condensing in equal molecular proportions alkylamino substiacids and having a constitution corresponding to the formula carboxylic acid and R an alkylamino substituted aromatic radical, which products are after being dried and pulverized slightly colored powders, which yield, when condensed with a further molecule of an aromatic oxycarboxylic acid leucotriphenylmethane bodies capable of being converted by oxidation into mordant dyestuffs, substantially as described.

being converted by oxidation into mor'dant ized slightly colored powders, which yield,

tuted aldehydes and aromatic oxycarboxylic I Where R is' the radical of an aromatic oxy- I obtained by condensing in equal molecular proportions paradiethyl-aminobenzaldehyde with s-xylenol-ortho-ca-rboxylic acid, having a constitution corresponding to the formula; I \/N(CH5 )g veriz'ed a slightly colored powder which 15 yields, when condensed with a further molecule of ortho-cresotinic acid, a leuco-triphen- -ylmethane body capable of being converte by oxidation into a mordant dyestufi producing on chrome mordanted Wool violet 20 shades.

In testimony whereof I have hereunto set my hand in the presence of two subscribing 'tnesses. i W1 MAX WE'ILER [1 s.] COOK CHOH Witnesses:

om CHAS. J. WRIGHT,-

which product is after being dried and pul- ALBERT NUFER.

flve'cents each, by addressing the Commissioner of Patents, Washington, D. 6.

Copies of this pstent may be obtained for I It is hereby certified that in Letters Patent No. 1,082,574, granted December 30, 1913, upon the application of Max Weiler of Elberfeld, Germany, for an improvement in The Manufacture and Production of Oxycerboxydiarylcarbinols, an error appearsin the printed specification requiring correction as follows: Page 2, line 2, for the word carboxyphenyldiethyamidophenylcarbinol tread ca/rboai rf phenyldiethylam'idophenylcarbinol; and thatthe said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Qfice. p V

Signed and sealed this eme y :of March, A. 1)., 1914.

' .n-r. NEWTON,

Actingflomm'iamkzmr of Patents. 7

Correction in Letters Patent No. 1,082,574. 

